DE3768123D1 - METHOD FOR PRODUCING HOMOALLYL ALCOHOLS. - Google Patents
METHOD FOR PRODUCING HOMOALLYL ALCOHOLS.Info
- Publication number
- DE3768123D1 DE3768123D1 DE8787302908T DE3768123T DE3768123D1 DE 3768123 D1 DE3768123 D1 DE 3768123D1 DE 8787302908 T DE8787302908 T DE 8787302908T DE 3768123 T DE3768123 T DE 3768123T DE 3768123 D1 DE3768123 D1 DE 3768123D1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- chem
- alkyl
- hydrogen
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 HOMOALLYL ALCOHOLS Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical class OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/44—Metal derivatives of an hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II <CHEM> wherein: X<1>, X<2> and X<3> are independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C1 to C6 alkyl, C1 to C6 haloalkyl, and haloaryl; and R<1>, R<2>, R<3> and R<4> are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R<3> and R<4> is as hereinbefore defined and R<1> and R<2> form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene of formula IV in the presence of an optically-active organometallic catalyst. <CHEM> Furthermore, the compound of formula II can be isomerised to the allylic alcohol of formula I with retention of optical purity. <CHEM> n
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPH534986 | 1986-04-07 | ||
| EP87302908A EP0241235B1 (en) | 1986-04-07 | 1987-04-02 | Process for the preparation of homoallyl alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3768123D1 true DE3768123D1 (en) | 1991-04-04 |
Family
ID=3771540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787302908T Expired - Fee Related DE3768123D1 (en) | 1986-04-07 | 1987-04-02 | METHOD FOR PRODUCING HOMOALLYL ALCOHOLS. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4933511A (en) |
| EP (1) | EP0241235B1 (en) |
| JP (1) | JPS638346A (en) |
| AT (1) | ATE61035T1 (en) |
| AU (1) | AU597042B2 (en) |
| DE (1) | DE3768123D1 (en) |
| GB (2) | GB2188633A (en) |
| HU (1) | HUT43312A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0714898B2 (en) * | 1988-07-28 | 1995-02-22 | 高砂香料工業株式会社 | Process for producing optically active α-hydroxycarboxylic acid ester |
| US5258529A (en) * | 1989-06-22 | 1993-11-02 | Sumitomo Chemical Company, Limited | Process for producing propargylcarbinol compounds |
| JPH06263652A (en) * | 1993-03-11 | 1994-09-20 | Central Glass Co Ltd | Production of optically active halogenated hydroxyolefins |
| USRE36718E (en) * | 1993-06-29 | 2000-05-30 | Kaneka Corporation | Optically active aminoalcohol derivatives and method of producing same |
| CN1116424A (en) * | 1993-09-20 | 1996-02-07 | 钟渊化学工业株式会社 | Process for producing 3-amino-2-hydroxy-1-propanol derivative |
| JP3337311B2 (en) * | 1994-03-11 | 2002-10-21 | 高砂香料工業株式会社 | Novel oxo-titanium complex, method for producing the same, and method for producing β-hydroxyketone or α-hydroxycarboxylic acid ester using the complex |
| JPH0977760A (en) * | 1995-07-10 | 1997-03-25 | Kanegafuchi Chem Ind Co Ltd | Production of 2-substituted optically active 2,3-dihydro-4h-pyran-4-one |
| SG81898A1 (en) * | 1995-08-11 | 2001-07-24 | Sumitomo Chemical Co | Olefin polymerization catalyst component, olefin polymerization catalyst and process for producing olefin polymer |
| US6090950A (en) * | 1996-08-23 | 2000-07-18 | Zeeland Chemicals, Inc. | Chiral hydride complexes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960973A (en) * | 1974-06-28 | 1976-06-01 | Phillips Petroleum Company | Alkenol production |
| DE2542377C3 (en) * | 1974-10-03 | 1980-10-02 | Kuraray Co., Ltd., Kurashiki, Okayama (Japan) | !, l.l-Trihalogen ^ -methyl-S-penten-2-ols and process for their preparation |
| US4117247A (en) * | 1974-10-03 | 1978-09-26 | Kuraray Co., Ltd. | Preparation of 1,1,1-trihalogeno-4-methyl-3-penten-2-ol |
| DE3023488A1 (en) * | 1980-06-24 | 1982-01-07 | Dynamit Nobel Ag, 5210 Troisdorf | Herbicide synergist and insecticide intermediate prodn. - 1,1,1-tri:chloro-2-hydroxy-4-methyl-3-pentene by isomerisation of 4-pentene deriv. produced by condensn. of chloral with isobutene |
| HU187819B (en) * | 1982-12-13 | 1986-02-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing trichloromethyl-carbinols |
| US4601994A (en) * | 1985-06-21 | 1986-07-22 | The Dow Chemical Company | Method for preparing supported TiIII catalysts |
| US4659685A (en) * | 1986-03-17 | 1987-04-21 | The Dow Chemical Company | Heterogeneous organometallic catalysts containing a supported titanium compound and at least one other supported organometallic compound |
-
1987
- 1987-03-24 AU AU70590/87A patent/AU597042B2/en not_active Ceased
- 1987-04-02 EP EP87302908A patent/EP0241235B1/en not_active Expired - Lifetime
- 1987-04-02 GB GB08707914A patent/GB2188633A/en not_active Withdrawn
- 1987-04-02 DE DE8787302908T patent/DE3768123D1/en not_active Expired - Fee Related
- 1987-04-02 AT AT87302908T patent/ATE61035T1/en not_active IP Right Cessation
- 1987-04-06 HU HU871453A patent/HUT43312A/en unknown
- 1987-04-06 JP JP62083102A patent/JPS638346A/en active Pending
- 1987-04-07 US US07/035,340 patent/US4933511A/en not_active Expired - Fee Related
-
1989
- 1989-11-02 GB GB8924714A patent/GB2224735A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ATE61035T1 (en) | 1991-03-15 |
| JPS638346A (en) | 1988-01-14 |
| AU597042B2 (en) | 1990-05-24 |
| GB2188633A (en) | 1987-10-07 |
| EP0241235B1 (en) | 1991-02-27 |
| AU7059087A (en) | 1987-10-08 |
| HUT43312A (en) | 1987-10-28 |
| GB8707914D0 (en) | 1987-05-07 |
| US4933511A (en) | 1990-06-12 |
| GB2224735A (en) | 1990-05-16 |
| EP0241235A2 (en) | 1987-10-14 |
| GB8924714D0 (en) | 1989-12-20 |
| EP0241235A3 (en) | 1988-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |